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I’m not sure if it’s what was being thought about, but the ‘save Kennedy’ time travel thing happened at the start of Red Dwarf VII. Actually a cool take on it given the usual broad comedy, they saved Kennedy from assassination, but the future became worse because mobsters could find blackmail leverage against Kennedy in later years because of his…proclivities.

So the gang ended up allowing Kennedy to go back in time and shoot himself so he could die an inspirational hero, instead of becoming a fallen one.

With all respect to y’all and the scion of the Great Bird, but there is definitely one culture that it was proven that Kirk did more harm than good, in violating the Prime Directive: The Mirror Universe.

From DS9’s forays into it, it was shown that Kirk’s influencing Spock in his cray-cray revolution to topple the Empire only made the Klingons (acting like spoiled, Old Forehead toffs) and the Bajorans/Cardassians the power in the new boogie groove… with humans as a lower-caste species. It’s not freedom when all of your enemies see your nobility as vulnerability, with one man’s secret weapon still making him as much of a dictator as anyone in the Empire.

If you disagree, say so — even though it’s a digression from TOS goodness.